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Synthesis of vulpinic acids from dimethyl tartrate

✍ Scribed by Brice Nadal; Pierre Thuéry; Thierry Le Gall

Book ID
104096394
Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
800 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

A series of vulpinic acids differing by the aryl or heteroaryl groups placed in the ester a-position were prepared by Suzuki-Miyaura cross-coupling involving a common iodide and the corresponding aryl boronates. The preparation of the iodide precursor from (+)-dimethyl L-tartrate required four steps: the esterification of one hydroxyl group, a Dieckmann cyclization allowing the construction of the tetronic acid moiety, a dehydration leading to the installation of the exocyclic double bond and lastly, an N-iodosuccinimide-mediated iodation of the alkene obtained.

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